Isopropanol → HCID 178465413, compound

HRID 345259Notes

Reaction equation

HRID 345259 reaction equation
[N+:1]([C:4]1[CH:57]=[CH:56][CH:55]=[CH:54][C:5]=1[CH2:6][O:7][C:8]([CH:10]([PH:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[N:11]1[CH:14]([CH2:15][CH2:16][OH:17])[CH:13]([CH:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])=[O:22])[CH3:19])[C:12]1=[O:34])=[O:9])([O-:3])=[O:2].CC(C)=[O:60].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O.C(Cl)Cl>[N+:1]([C:4]1[CH:57]=[CH:56][CH:55]=[CH:54][C:5]=1[CH2:6][O:7][C:8]([CH:10]([PH:35]([C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)([C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1)[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[N:11]1[C@@H:14]([CH2:15][C:16]([OH:60])=[O:17])[C@H:13]([CH:18]([NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[N+:31]([O-:33])=[O:32])=[O:22])[CH3:19])[C:12]1=[O:34])=[O:9])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 131709961Jones' reagentHCID 178465410HCID 178465410, compound

Product 1

HCID 178465413HCID 178465413, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

1-(o-Nitrobenzyloxycarbonyltriphenylphosphoranylmethyl)-3-(1-o-nitrobenzyloxycarbonylaminoethyl)-4-(2'-hydroxyethyl)-2-azetidinone (0.1582 g, 0.20 mmol) (cf. Example 43, Step I) is dissolved in 5 ml acetone cooled to 0°. Jones Reagent (0.12 ml, 4N solution) is added dropwise over 3 minutes and the resulting solution is stirred at 0° for 10 minutes. Isopropanol (0.05 ml) is added and the mixture stirred for another 2 minutes. The reaction mixture is diluted with CH2Cl2 and filtered. The filtrate is washed with saturated NaCl aqueous solution, dried and evaporated to give 0.132 g of crude acid which is used without further purification in the next step.

Workup

  1. temperaturecooled to 0°
  2. stirringthe mixture stirred for another 2 minutes
  3. filtrationfiltered
  4. washThe filtrate is washed with saturated NaCl aqueous solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0a1b08d8462f42b4a92dbf0d7967cc62
Source dataset
uspto-grants-1991_10
Patent number
US05055573

Reaction notes

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